A “click chemistry” approach to the straightforward synthesis of new 4-aryl-1,2,3-triazolocarbanucleosides

Abstract

Dedicated to Professor Benito Alcaide on the occasion of his 60th birthday AbstractThe synthesis and biological evaluation as antiviral agents of a series of racemic 4-aryl-1,2,3-triazolyl carbanucleosides of type (±)-10/(±)-11 related to the broad spectrum antiviral agent ribavirin 1 are described. These compounds were produced using a "click chemistry" strategy starting from readily available protected alcohol 13b. The synthetic approach made use of olefinbased organic reactions for the stereoselective construction of the appropriately functionalized cyclopentane ring moiety followed by copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition of azides and alkynes for the regioselective construction of the heterocyclic triazole moiety.

Synthesis and biological activity of potential antiviral compounds through 1,3-dipolar cycloadditions; Part 1: general aspects and reactions of azides

“…A simple structural modification of compounds 23 have been proposed by Spanish authors that prepared diastereoisomeric 2-azido-4-(hydroxymethyl)cyclopentan-1-ols that were used to synthesize a series of racemic 4-aryl-1,2,3-triazolyl carbanucleosides through a "click chemistry" strategy. 32 The target compounds were tested against a variety of viruses but unfortunately none of them displayed a significant inhibitory activity. A series of trisubstituted 1,2,3-triazole purine nucleosides were efficiently synthesized via Huisgen 1,3-dipolar cycloaddition in good yields from but-2-yne-1,4-diol and ethyl 2-azidoacetate.…”